title: Isolation of a sultone as an unusual acetolysis product.
abstract: Acetolysis of methyl 5,6-di-O-acetyl-2,3-O-isopropylidene-β-L-gulofuranoside has yielded a sultone, 4-(1,2,5,6-tetra-O-acetyl-β-L-gulofuranos-3-yl)-6-methyl-1,2-oxathiin 2,2-dioxide (2) whose structure was determined by X-ray diffraction. (1)H and (13)C NMR spectral properties of 2 are presented together with a rationale for its formation. Preparation and properties of the related α-d-mannofuranos-3-yl compound 4 are described.
authors.affiliation: School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia.
authors.forename: Donald C
authors.initials: DC
authors.lastname: Craig
authors.forename: John D
authors.initials: JD
authors.lastname: Stevens
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009282:Naphthalenesulfonates / Q000138:chemical synthesis* / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D009282:Naphthalenesulfonates; C016768:naphthosultone